WO1991017739A1 - Colorants d'oxydation pour fibres de keratine - Google Patents

Colorants d'oxydation pour fibres de keratine Download PDF

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Publication number
WO1991017739A1
WO1991017739A1 PCT/EP1991/000874 EP9100874W WO9117739A1 WO 1991017739 A1 WO1991017739 A1 WO 1991017739A1 EP 9100874 W EP9100874 W EP 9100874W WO 9117739 A1 WO9117739 A1 WO 9117739A1
Authority
WO
WIPO (PCT)
Prior art keywords
hair
formula
oxidation
salts
indolines
Prior art date
Application number
PCT/EP1991/000874
Other languages
German (de)
English (en)
Inventor
Günther KONRAD
Iduna Matzik
Edgar Lieske
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
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Application filed by Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Priority to EP91909057A priority Critical patent/EP0530229B1/fr
Priority to US07/949,851 priority patent/US6719811B1/en
Priority to PL91296708A priority patent/PL166189B1/pl
Priority to CA002083378A priority patent/CA2083378A1/fr
Priority to KR1019920702879A priority patent/KR0175948B1/ko
Priority to DE59105887T priority patent/DE59105887D1/de
Priority to JP3508741A priority patent/JP2996724B2/ja
Publication of WO1991017739A1 publication Critical patent/WO1991017739A1/fr
Priority to NO923518A priority patent/NO180566C/no
Priority to FI925241A priority patent/FI100021B/fi

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair

Definitions

  • the invention relates to the use of indoline derivatives, in particular 5,6-dihydroxyindolines, as the oxidation dye precursor for the production of oxidation colorants for keratin fibers, in particular for human hair.
  • the natural hair dyes are formed in the course of their biosynthesis by oxidative polymerization of 5,6-dihydroxyindole.
  • 5,6-dihydroxyindole is extremely unstable both in free form and in the form of its salts in aqueous solution and, in the presence of atmospheric oxygen, very quickly forms insoluble, colored oxidation and polymerization products which can no longer be fixed on the hair itself . Therefore, all attempts to use the 5,6-dihydroxyindole itself or its salts in dye preparations have led to unsatisfactory and commercially unsuitable hair dye compositions.
  • R 1 , R--, R - * - * , R 4 and R- "independently of one another are hydrogen or alkyl groups with 1 - 4 C atoms or R ⁇ and R-- also together with the oxygen atoms to which they are attached represent an alkylenedioxy group with 1 to 4 carbon atoms, or their salts as oxidation dye precursors for producing oxidation colorations.
  • 5,6-Dihydroxyindoline ie the indole derivative of the formula I, in which R 1 , R 2 , R 3 , R 4 and R 5 is hydrogen
  • R 1 , R 2 , R 3 , R 4 and R 5 is hydrogen
  • derivatives of 5,6-dihydroxyindole also form dyes similar to melanin under oxidation conditions.
  • the alkyl-substituted indolines of formula I preferably those in which one of the groups R, R 2 and R 3 is a methyl group and the other hydrogen are, are suitable as oxidation dye precursors for the preparation of storage-stable dyeing preparations.
  • the 5,6-dimethoxyindoline and the 5,6-dihydroxyindoline are known in the literature, their production is e.g. in J. Chem. Soc. (C), 1967, pages 1424 to 1427.
  • the alkyl-substituted indolines of the formula I can be prepared in an analogous manner from the correspondingly substituted 5,6-dihydroxyindoles or alkoxyindoles by catalytic hydrogenation.
  • Another process for the preparation of 5,6-dihydroxyindolines from 5,6-dimethoxy indoles by reduction with sodium cyanoborohydride and cleavage of the methoxy groups in concentrated hydrochloric acid is in the Journal of Medicinal Chemistry, 1978, Vol 21, No. 6, page 553.
  • the indolines of the formula I to be used according to the invention are preferably used as the only oxidation dye precursors. They can be used in free form or in the form of their salts, preferably as hydrochlorides, hydrobromides, sulfates, phosphates, acetates, propionates, lactates or citrates.
  • oxidation dye precursors and optionally also known substantive dyes can also be used together with the indolines of the formula I to modify the color shades.
  • indolines of the formula I and their salts are also well suited for use as coupler components in oxidation hair colorants containing conventional developer compounds.
  • a further subject of the invention are therefore hair colorants containing oxidation dye precursors in a carrier, characterized in that indolines of the formula I or their salts and the developer compounds customary for oxidation hair colorants are contained as coupler components.
  • the indolines of the formula I modify the dyeings which can be achieved with the developer compounds solely by self-coupling and lead to intense, brilliant dark brown to blue-black shades.
  • Such hair colorants preferably contain a weakly basic carrier.
  • Suitable developer compounds are, for example, p-phenylene diamine, p-tolylene diamine, 2-chloro-p-phenylene diamine, N-methyl-p-phenylene diamine, N, N-diethyl-p-phenylene diamine, N- ( ⁇ -hydroxyethyl) - p-phenylenediami ⁇ , NN-dimethyl-p-phenylenediami ⁇ , N, N-bis- (ß-hydroxyethyl) -p-phenylenediamine, 2,5-diaminobenzyl alcohol and other compounds of the type mentioned, which also contain one or more NH2- May contain groups, NHR groups or NR2 groups, in which R is alkyl groups with 1 to 4 carbon atoms or hydroxyalkyl groups with 2 to 4 carbon atoms, and p-aminophenols, l-amin
  • the indolines of the formula I are used as couplers for modifying the shade of the developer compounds mentioned, they are used in amounts of 0.1 to 10 millimoles per 100 g of the hair dye. They are usually used in approximately molar amounts based on the developer substances used. If molar use has also proven to be expedient, an excess of individual oxidation dye precursors is also not disadvantageous.
  • indoles of the formula I are uniform chemical compounds; on the contrary, these can also be mixtures of the indoles of the formula I to be used according to the invention or their salts.
  • the oxidation dye precursors are incorporated in a suitable carrier.
  • suitable carriers are e.g. Creams, emulsions, gels or also surfactant-containing, foaming solutions (shampoos), foam aerosols or other preparations which are suitable for use on the hair.
  • Such carriers contain finishing and dyeing aids which increase the stability of the preparations and improve the result of the coloring.
  • Such additives are primarily surfactants, e.g.
  • Soaps in particular the alkali or alkanolamine soaps of linear C 1 -C 4 fatty acids, in particular oleic acid,
  • Anionic surfactants for example fatty alcohol sulfates and fatty alcohol polyglycol ether sulfates, alkane sulfonates, alpha-olefin sulfonates or oleic acid sulfonates, preferably in the form of the alkali metal, ammonium or alkanolammonium salts - Cationic surfactants, for example alkyl (Ci2-Ci8) -trimethyl-ammonium chloride, alkyl (Ci2-Ci8) -dimethyl-benzyl-ammonium salts, cetyl-pyridinium chloride, 2-hydroxydodecyl-hydroxyethyl-dimethylammonium chloride
  • zwitterionic surfactants such as Alkyl- (Ci2-Ci8) -dimethyl-ammonium-glycinate, cocoacylaminopropyl-dimethyl-ammonium-glycinate, or imidazolinium betaines
  • photere tensides e.g. N-dodecylaminoacetic acid, N-cetylaminopropionic acid, gamma-laurylamino-butyric acid and
  • Nonionic surfactants in particular addition products of 5-30 mol ethylene oxide with fatty alcohols, with alkylphenols, with fatty acids, with fatty acid alkanolamides, with fatty acid partial glycerides, with fatty acid sorbitan partial esters or with fatty acid methylglucoside partial esters, furthermore alkylglucosides, amine oxides and fatty acids acid polyglycerol esters.
  • water-soluble, thickening polymers e.g. Cellulose ethers such as carboxymethyl cellulose, hydroxyethyl cellulose, methyl cellulose, methyl hydroxypropyl cellulose, starch and starch ether, vegetable gum, guar gum, agar agar, alginates, xanthan gum or synthetic water-soluble polymers.
  • hydrocolloids e.g. Cellulose ethers such as carboxymethyl cellulose, hydroxyethyl cellulose, methyl cellulose, methyl hydroxypropyl cellulose, starch and starch ether, vegetable gum, guar gum, agar agar, alginates, xanthan gum or synthetic water-soluble polymers.
  • Antioxidants e.g. Ascorbic acid, Na2S03,
  • - buffer substances e.g. Ammonium chloride and ammonium sulfates
  • Hair cosmetic auxiliaries for example water-soluble cationic polymers, protein derivatives, glucose, D-panthenol, cholesterol, vitamins or plant extracts,
  • Leveling aids e.g. Urazole, hexahydropyrimidin-2-one, imidazole, 1,2,4-triazole or iodides, e.g. Sodium or potassium iodide
  • the hair colorants according to the invention can be used in the weakly acidic, neutral or weakly alkaline pH range.
  • a preferred embodiment of the invention is hair colorants containing oxidation dye precursors in a carrier, the oxidation dye precursors indolines of the formula I or their salts in an amount of 0.1-20 millimoles per 100 g of the hair dye and a gel with a carrier Content of 1 - 20 wt .-% of a soap or an oil-in-water emulsion with a content of 1 - 25 wt .-% of a fat component and 0.5 - 30 wt .-% of an emulsifier from the group of the anionic , non-ionic, cationic, zwitterionic or a pholytic Ten ⁇ side contain.
  • Suitable neutral or weakly acidic carriers for the dye preparation are preferably oil-in-water cream emulsions with a content of fatty alcohols having 12-22 carbon atoms, preferably cetyl and stearyl alcohol as the fat component and nonionogenic zwitterionic or cationic emulsifiers, preferably addition products of 10-30 moles of ethylene oxide with cetyl and stearyl alcohol, which are optionally adjusted to a pH of 2.5-4 by adding citric acid or other weak acids.
  • the indoline of the formula I to be used according to the invention is incorporated into this emulsion in an amount of 2-20 millimoles per 100 g.
  • Gels or oil-in-water emulsions are preferred as weakly basic carriers for the dye preparation.
  • Suitable gels contain 1-20% by weight of a soap, preferably ammonium oleate, preferably additionally 1-10% by weight of a nonionic emulsifier and 5-20% by weight of a fatty alcohol with 12-22 C atoms as surface-active substances as a fat component.
  • Suitable oil-in-water emulsions contain 1-25% by weight of a fat component, preferably a fatty alcohol with 12-22 C atoms, and 0.5-30% by weight of an emulsifier, preferably 1-20% by weight .-% of an anionic, non-ionic, zwitterionic or ampholytic surfactant.
  • the oxidative development of the color can in principle be carried out with atmospheric oxygen.
  • a chemical oxidizing agent is preferably used, especially when a lightening effect on the hair is desired in addition to the coloring.
  • the oxidation can either be initiated immediately before use of the dye preparation by mixing with an oxidizing agent or only on the hair.
  • the dye preparation is mixed with an oxidizing agent, preferably with hydrogen peroxide solutions or with hydrogen peroxide addition products on urea, melamine or sodium borate, and applied to the hair after a short exposure time, the oxidation process and the development of the dye then during the exposure time is accomplished on the hair.
  • an oxidizing agent preferably with hydrogen peroxide solutions or with hydrogen peroxide addition products on urea, melamine or sodium borate
  • Suitable oxidizing agents are preferably hydrogen peroxide solutions or dispersions of potassium or ammonium peroxydisulfate or water-soluble periodates. These dispersions can have a composition similar to that of the carriers described above for neutral or weakly acidic dye preparations in the form of a cream emulsion.
  • the separate application of the oxidizing agent to the hair requires more care and practice and is therefore preferably suitable for commercial use by the hairdresser.
  • a coloring cream emulsion of the following composition was produced:
  • the coloring cream was applied to strands of hair 15 cm in length and about 2 g in weight from untreated, standardized, 80% gray human hair and left to act at 25 ° C. for 20 minutes.
  • the oxidizing agent dispersion was then applied to the same strands of hair and left to act for 20 minutes.
  • the tresses were then washed with a conventional sha poo, rinsed with water and dried.
  • a medium brown color tone and very good gray coverage of the test strand were achieved.
  • the light fastness, fastness to rubbing and resistance to permanent wave treatment were very good.
  • a coloring cream emulsion of the following composition was produced:
  • the ingredients were mixed together in order. After adding the 5,6-dihydroxyindoline and the ammonium sulfate (buffer), the pH of the emulsion was first adjusted to 9.5 with concentrated ammonia solution, and the mixture was then made up to 100 g with water. The oxidative development of the color was carried out with 3% hydrogen peroxide solution as the oxidizing agent. For this purpose, 100 g of the emulsion were mixed with 50 g of hydrogen peroxide solution (3%) and mixed.
  • the coloring cream was standardized on strands approx. 5 cm long, applied to 90% gray, but not specially pretreated human hair and left there at 27 ° C. for 30 minutes. After the dyeing process had ended, the hair was rinsed, washed out with a customary shampoo and then dried.
  • the color was characterized by very good fastness properties (e.g. light fastness, fastness to rubbing, cold wave fastness, wash fastness).
  • Hair colorants according to the invention were produced in the form of a hair color cream emulsion of the following composition:

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
  • Indole Compounds (AREA)
  • Materials For Medical Uses (AREA)
  • Pyrrole Compounds (AREA)
  • Coloring (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

En utilisant des indolines de formule (I), dans laquelle R?1, R2, R3, R4 et R5¿ représentent, indépendamment les uns des autres, de l'hydrogène ou des groupes alkyles de 1 à 4 atomes de carbone, ou R4 et R5 représentent, conjointement avec les atomes d'oxygène auxquels ils sont liés, un groupe alkylène-dioxy de 1 à 4 atomes de carbone, ou leurs sels comme avant-produits pour des colorants d'oxydation, on obtient des teintures pour cheveux brunes naturelles. Les indolines de formule (I) conviennent également comme coupleurs dans les colorants d'oxydation pour cheveux ayant une teneur en composés révélateurs courants. Elles entraînent une modification des nuances pouvant être obtenues avec le révélateur. L'application s'effectue dans des supports courants, par exemple sous forme de gels ou d'émulsions, lesquels sont mélangés, de préférence avant l'application ou sur les cheveux, avec un agent d'oxydation, pour le développement du colorant.
PCT/EP1991/000874 1990-05-19 1991-05-10 Colorants d'oxydation pour fibres de keratine WO1991017739A1 (fr)

Priority Applications (9)

Application Number Priority Date Filing Date Title
EP91909057A EP0530229B1 (fr) 1990-05-19 1991-05-10 Colorants d'oxydation pour fibres de keratine
US07/949,851 US6719811B1 (en) 1990-05-19 1991-05-10 Oxidation colorants for keratin fibers
PL91296708A PL166189B1 (pl) 1990-05-19 1991-05-10 Srodek do barwienia wlosów PL PL PL PL PL
CA002083378A CA2083378A1 (fr) 1990-05-19 1991-05-10 Colorants d'oxydation pour les fibres keratiniques
KR1019920702879A KR0175948B1 (ko) 1990-05-19 1991-05-10 케라틴 섬유용 산화염료
DE59105887T DE59105887D1 (de) 1990-05-19 1991-05-10 Oxidationsfärbemittel für keratinfasern.
JP3508741A JP2996724B2 (ja) 1990-05-19 1991-05-10 ケラチン繊維用の酸化染料
NO923518A NO180566C (no) 1990-05-19 1992-09-10 Anvendelse av indoliner som oksydasjonsfargestoff-forprodukter samt hårfargemiddel inneholdende forproduktene
FI925241A FI100021B (fi) 1990-05-19 1992-11-18 Keratiinikuitujen hapetusväriaineet

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4016177A DE4016177A1 (de) 1990-05-19 1990-05-19 Oxidationsfaerbemittel fuer keratinfasern
DEP4016177.3 1990-05-19

Publications (1)

Publication Number Publication Date
WO1991017739A1 true WO1991017739A1 (fr) 1991-11-28

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ID=6406795

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1991/000874 WO1991017739A1 (fr) 1990-05-19 1991-05-10 Colorants d'oxydation pour fibres de keratine

Country Status (17)

Country Link
US (1) US6719811B1 (fr)
EP (1) EP0530229B1 (fr)
JP (1) JP2996724B2 (fr)
KR (1) KR0175948B1 (fr)
AT (1) ATE124252T1 (fr)
CA (1) CA2083378A1 (fr)
CZ (1) CZ280081B6 (fr)
DE (2) DE4016177A1 (fr)
DK (1) DK0530229T3 (fr)
ES (1) ES2073754T3 (fr)
FI (1) FI100021B (fr)
HU (1) HU213250B (fr)
NO (1) NO180566C (fr)
PL (1) PL166189B1 (fr)
SK (1) SK278595B6 (fr)
WO (1) WO1991017739A1 (fr)
YU (1) YU47444B (fr)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993005018A1 (fr) * 1991-09-12 1993-03-18 L'oreal Composition tinctoriale a base de derives d'hydroxyindoline
WO1993009759A1 (fr) * 1991-11-19 1993-05-27 Henkel Kommanditgesellschaft Auf Aktien 5,6-dihydroxyindolines utilisees comme adjuvants a des formulations de teintures pour cheveux
WO1993013744A1 (fr) * 1992-01-16 1993-07-22 L'oreal Produits indoliniques, leurs procedes de preparation et leur utilisation en cosmetique
WO1994003148A2 (fr) * 1992-08-05 1994-02-17 Henkel Kommanditgesellschaft Auf Aktien Agent bronzant pour la peau
WO1999066890A1 (fr) * 1998-06-23 1999-12-29 Henkel Kommanditgesellschaft Auf Aktien Colorant pour colorer des fibres keratiniques
WO2001045655A1 (fr) * 1999-12-20 2001-06-28 Henkel Kommanditgesellschaft Auf Aktien Colorant solide pour fibres de keratine
US6569211B2 (en) 1991-11-19 2003-05-27 Henkel Kommanditgesellschaft Auf Aktien 5,6-dihydroxyindolines as additives for hair dyeing preparations
US6790240B2 (en) 1999-12-20 2004-09-14 Henkel Kommanditgesellschaft Aug Aktien Solid colorant for keratin fibers
US6797012B2 (en) 1999-12-20 2004-09-28 Henkel Kommanditgesellschaft Auf Aktien Solid colorant for keratin fibers
US7204856B2 (en) 1999-12-20 2007-04-17 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Shaped bodies for forming cosmetic preparations
WO2007141164A2 (fr) * 2006-06-02 2007-12-13 Henkel Ag & Co. Kgaa Dispositif d'application pour utiliser un liquide d'application sur des fibres de kératine

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DE4208297A1 (de) * 1992-03-16 1993-09-23 Henkel Kgaa Faerben von keratinischen fasern mit indolinen unter metallkatalyse
DE19714370A1 (de) † 1997-04-08 1998-10-15 Henkel Kgaa Wäßrige pflegende Haut- und Haarbehandlungsmittel
DE19732975A1 (de) * 1997-07-31 1999-02-04 Henkel Kgaa Färbemittel
DE19930927A1 (de) * 1999-07-06 2001-01-11 Henkel Kgaa Neue Farbstoffe und Färbemittel
DE10020887A1 (de) 2000-04-28 2001-10-31 Henkel Kgaa Neue Verwendung von Zuckertensiden und Fettsäurepartialglyceriden
DE10045856A1 (de) 2000-09-14 2002-03-28 Henkel Kgaa Haarfärbemittel mit Indigoderivaten
DE10100938A1 (de) 2001-01-10 2002-07-11 Henkel Kgaa Indol-/Indolin-Hybridfarbstoffe und -hybridfarbstoffvorprodukte
JP4312980B2 (ja) 2001-12-26 2009-08-12 花王株式会社 染毛剤組成物
AU2003218991A1 (en) * 2002-03-01 2003-09-16 Henkel Kommanditgesellschaft Auf Aktien Colouring agents
DE10354812A1 (de) * 2003-11-21 2006-08-17 Henkel Kgaa Verfahren zur Färbung keratinhaltiger Fasern
WO2005082321A1 (fr) * 2004-02-27 2005-09-09 Henkel Kommanditgesellschaft Auf Aktien Utilisation de derives d'amidon cationiques pour conserver les couleurs
US7267745B2 (en) * 2004-09-03 2007-09-11 Voith Fabrics, Inc. Papermakers felt having a point-bonded web layer formed of coarse fibers
DE102004062702A1 (de) * 2004-09-16 2006-03-23 Henkel Kgaa Farbverändernde Mittel mit Moringa Extrakt
DE102004045414A1 (de) 2004-09-18 2006-03-30 Henkel Kgaa Verfahren zur modischen Farbveränderung keratinhaltiger Fasern
DE102004062428A1 (de) 2004-12-20 2006-07-06 Henkel Kgaa Haarfarbveränderndes Shampoo
DE102005011924A1 (de) 2005-03-14 2006-10-19 Henkel Kgaa Neue Farbstoffe und Färbemittel mit speziellen Carbonylverbindungen
DE102005013067A1 (de) * 2005-03-18 2006-10-19 Henkel Kgaa Ammoniakfreies Oxidationsfärbemittel zur Färbung keratinhaltiger Fasern mit Luftsauerstoff als einzigem Oxidationsmittel
DE102005025494A1 (de) 2005-06-01 2006-12-14 Henkel Kgaa Mehrstufiges Färbeverfahren für keratinische Fasern
DE102005043187A1 (de) 2005-09-09 2007-03-15 Henkel Kgaa Polymere mit kleiner Molmasse
DE102005057183A1 (de) 2005-11-29 2007-06-06 Henkel Kgaa Biomimetische Melaninpigmente
DE102005061727A1 (de) 2005-12-21 2007-06-28 Henkel Kgaa Tönungsmittel auf Basis von Pflanzenfarbstoffen
DE102005062356A1 (de) 2005-12-23 2007-06-28 Henkel Kgaa Verringerung der Haaralterung
DE102006061555A1 (de) 2006-12-27 2008-07-03 Henkel Kgaa Synergistische Kombination von Seidenproteinen und ausgewählten Metallen
DE102007027862A1 (de) 2007-06-13 2008-12-24 Henkel Ag & Co. Kgaa Verfahren zur Abfüllung haarfarbverändernder Mittel
DE102007045974A1 (de) 2007-09-25 2009-04-09 Henkel Ag & Co. Kgaa Biotin und Kieselsäure gegen Haaralterung
DE102007061505A1 (de) 2007-12-18 2009-06-25 Henkel Ag & Co. Kgaa Tönungs-Gel-Schaum
DE102008032851A1 (de) 2008-07-14 2010-01-21 Henkel Ag & Co. Kgaa Mittel mit Naturfarbstoff
JP2010070549A (ja) * 2008-08-19 2010-04-02 Kao Corp 染毛剤組成物
KR101891495B1 (ko) 2018-01-16 2018-08-27 주식회사 머니브레인 사용자 발화 입력에 대한 대화 응답 후보를 표시하도록 하는 디스플레이 제어 방법, 컴퓨터 판독가능 기록 매체 및 컴퓨터 장치
KR20190094080A (ko) 2018-10-19 2019-08-12 주식회사 머니브레인 사용자간 대화 세션에 대한 모니터링에 기초하여 능동적으로 주문 또는 예약 서비스를 제공하는 대화형 ai 에이전트 시스템, 방법 및 컴퓨터 판독가능 기록 매체
KR20190103927A (ko) 2018-10-25 2019-09-05 주식회사 머니브레인 보안 등과 관련된 서비스를, 사용자간 대화 세션에 대한 모니터링에 기초하고 대화 세션 또는 별도의 세션을 통해, 능동적으로 제공하는 대화형 ai 에이전트 시스템, 방법 및 컴퓨터 판독가능 기록 매체
KR20190056967A (ko) 2018-10-25 2019-05-27 주식회사 머니브레인 보안성을 강화한 의미-무관 사용자 성문 인증을 제공하는 방법, 대화형 ai 에이전트 시스템 및 컴퓨터 판독가능 기록 매체
KR20190094081A (ko) 2018-10-26 2019-08-12 주식회사 머니브레인 대화형 ai 에이전트 시스템을 위한 지식베이스의 시각화 방법 및 컴퓨터 판독가능 기록 매체
EP4154864A1 (fr) 2022-09-22 2023-03-29 Dr. Kurt Wolff GmbH & Co. KG Composition pour la pigmentation des fibres kératiniques, en particulier les cheveux humains

Citations (3)

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Cited By (17)

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WO1993005018A1 (fr) * 1991-09-12 1993-03-18 L'oreal Composition tinctoriale a base de derives d'hydroxyindoline
FR2681318A1 (fr) * 1991-09-12 1993-03-19 Oreal Composition tinctoriale a base de derives d'hydroxyindoline, procede de teinture des fibres keratiniques et nouveaux derives d'hydroxyindoline.
WO1993009759A1 (fr) * 1991-11-19 1993-05-27 Henkel Kommanditgesellschaft Auf Aktien 5,6-dihydroxyindolines utilisees comme adjuvants a des formulations de teintures pour cheveux
US6569211B2 (en) 1991-11-19 2003-05-27 Henkel Kommanditgesellschaft Auf Aktien 5,6-dihydroxyindolines as additives for hair dyeing preparations
WO1993013744A1 (fr) * 1992-01-16 1993-07-22 L'oreal Produits indoliniques, leurs procedes de preparation et leur utilisation en cosmetique
FR2686344A1 (fr) * 1992-01-16 1993-07-23 Oreal Produits indoliniques, leurs procedes de preparation et leur utilisation en cosmetique.
US5583234A (en) * 1992-01-16 1996-12-10 L'oreal Indoline-based products, processes for preparing them and their use in cosmetics
WO1994003148A3 (fr) * 1992-08-05 2000-09-08 Henkel Kgaa Agent bronzant pour la peau
WO1994003148A2 (fr) * 1992-08-05 1994-02-17 Henkel Kommanditgesellschaft Auf Aktien Agent bronzant pour la peau
WO1999066890A1 (fr) * 1998-06-23 1999-12-29 Henkel Kommanditgesellschaft Auf Aktien Colorant pour colorer des fibres keratiniques
WO2001045655A1 (fr) * 1999-12-20 2001-06-28 Henkel Kommanditgesellschaft Auf Aktien Colorant solide pour fibres de keratine
US6673123B2 (en) 1999-12-20 2004-01-06 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Solid colorant for keratin fibers
US6790240B2 (en) 1999-12-20 2004-09-14 Henkel Kommanditgesellschaft Aug Aktien Solid colorant for keratin fibers
US6797012B2 (en) 1999-12-20 2004-09-28 Henkel Kommanditgesellschaft Auf Aktien Solid colorant for keratin fibers
US7204856B2 (en) 1999-12-20 2007-04-17 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Shaped bodies for forming cosmetic preparations
WO2007141164A2 (fr) * 2006-06-02 2007-12-13 Henkel Ag & Co. Kgaa Dispositif d'application pour utiliser un liquide d'application sur des fibres de kératine
WO2007141164A3 (fr) * 2006-06-02 2008-01-31 Henkel Kgaa Dispositif d'application pour utiliser un liquide d'application sur des fibres de kératine

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CA2083378A1 (fr) 1991-11-20
KR0175948B1 (ko) 1999-03-20
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DK0530229T3 (da) 1995-11-06
YU86591A (sh) 1994-01-20
NO180566C (no) 1997-05-14
ES2073754T3 (es) 1995-08-16
FI100021B (fi) 1997-08-29
FI925241A0 (fi) 1992-11-18
NO180566B (no) 1997-02-03
US6719811B1 (en) 2004-04-13
JPH05507106A (ja) 1993-10-14
YU47444B (sh) 1995-03-27
DE59105887D1 (de) 1995-08-03
EP0530229A1 (fr) 1993-03-10
EP0530229B1 (fr) 1995-06-28
ATE124252T1 (de) 1995-07-15
SK278595B6 (en) 1997-11-05
FI925241A (fi) 1992-11-18
HU213250B (en) 1997-04-28
DE4016177A1 (de) 1991-11-21
JP2996724B2 (ja) 2000-01-11
NO923518D0 (no) 1992-09-10
PL166189B1 (pl) 1995-04-28
NO923518L (no) 1992-09-10
CS147691A3 (en) 1992-02-19
CZ280081B6 (cs) 1995-10-18
HU9203615D0 (en) 1993-03-29

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